Met My Match

I was working as a temp at a law firm in the early aughts. It was a pretty chill atmosphere. All of us temps were off away from the lawyers on a floor in a cube farm. The group of us could bullshit all day with each other. It was a mix of actors, people who wanted a taste of a firm before law school and those, like me, who were there for the paycheck unsure of the next step. These temp gigs could last for years if you let them, and this was my second long run at a firm while I figured out what I wanted to do.

Carolina had started a few weeks after I had and we'd been working together for just short of a year. I'd describe her as quiet and introverted. She was about 35 (I was 30) pretty, of Jamaican descent with a light skin tone (by the way, these last two points describe myself as well. Having been raised in the lily white suburbs, I'd never been with anyone remotely like myself -- nor many women at all for that matter). Carolina was a little chubby, but, being me, the fact that she had enormous tits and a bubble ass made the whole package all good. This is not to say that I was immediately attracted -- neither of us made ourselves conspicuous and for that first year she was just another person in the grind of monotonous temp paralegal work to me.

One day four or five of us were working in a conference room and we were idly chatting about what we would do after working at the firm. Carolina had mentioned that she wanted to write children's books. On my turn, I said I wanted to do stand-up comedy (I'd been doing it, on and off for about 4 years at that point. Eventually I'd realize I wasn't cut out for it). She kind of snorted derisively when I said it.

"Really?" she said.

"Yeah, you don't think I could do it?"

At that point she kind of shook her head and waved me off, seeing that this was probably going to lead to a fight in the workplace. Nobody wanted that.

I was taken aback by her condescension. After that I was torn between avoiding her and confronting her to show her that she was wrong. She'd gotten in my head.

A couple of weeks later we were leaving the building together and I brought it up.

"Why would you think I couldn't do stand up?"

She smirked, "Do YOU think you're funny?"

"I do. I mean, not always at work, but yeah."

"Ok, so why don't you make me laugh?"

"Uh, ok, do you want to get a drink?"

To this day I don't know where I got the balls to ask her out on the spot. Never before nor since have I done that without planning it out. She wasn't free that evening, but we got a drink a few nights later.

After that we went out a few times but neither of us really pushed it to go further than just hanging out. I think we were both waiting for the other person to make the move to something more serious.

We actually stopped dating after about three weeks and a month later one of the firm's vendors threw an afternoon into evening booze cruise in the harbor; I ended up getting quite buzzed. Carolina was there wearing tight white slacks and a black v-neck sweater that showed a hint of cleavage. This was near the end of my run at the firm and I'd given them notice so, in addition to the alcohol, I didn't give as much of a shit about consequences with this particular crowd. We hadn't been around each other much during the cruise but as the ship was pulling back into the pier, I spotted her coming out of the bathroom.

I wish I could remember more of this part of the conversation but it became apparent to me after a minute or two that this might go differently than our chaste dates had. Carolina let me know that she'd had a little too much to drink on the cruise and had just thrown up in the bathroom. I made sure she was going to be alright and walked with her off the boat and down the gangplank. On her way to the corner to hail a cab I stopped her.

"Look, I know we gave it a shot, but I've always been attracted to you. How would you like it if we hopped in a cab back to your place?"

"But, I, I just threw up... uhh." Carolina was unsure but smiling. She gave me a questioning look as if to ask if that was a deal breaker. She would turn away when talking so that I couldn't smell her breath.

"It doesn't bother me. I mean, look, we can wait to do anything until you can get refreshed." I know, I'm too suave for words.

"Okay, I guess." She still looked a little unsure.

I hailed us a cab. We were making idle chit chat about the passing buildings. While I was pointing out a place I used to work I casually reached over and caressed her right breast. It was a strange ride: we continued with small talk while our hands roamed over each others bodies. The cab was cramped and there wasn't much leg room, so my hands wandered from her tits down between her closed legs with the side of my hand up against her sex. She was doing the same thing with the pinky side of her hand against my dick. Although the conversation was tame our eye contact made clear we were both horny as hell. Eventually we got to her place and the driver, if he knew what was going on, made no indication he cared. I paid him and he drove off.

I had a raging hard on as we climbed up the three floors to her apartment, my eyes rarely straying from her generous swaying ass. Carolina's place was a studio with a high ceiling and was dimly lit romantically. When we got in she bee-lined to the bathroom telling me over her shoulder to take a seat at her kitchen table. I think I was probably grinning the entire time I sat there. It had been about six months since I'd last had sex with anyone and I couldn't wait to get to it. She took her time getting ready. She finally came out wearing only her black sweater showing a lot more cleavage than earlier. She walked into my arms as I stood up. There was a half second where we regarded each other and then we were making out: big, indulgent kisses like we were trying to devour each other. I reached down to grab her ass and her leg rode up my thigh pulling me into her. Her breasts were mashed against my chest and I was groping at the side of her right tit with my free hand. I realized then that the sweater was the only thing she was wearing. My dick was straining at my slacks as she ground her bare pussy against me.

We stepped back at each other sharing a "wow" look. The chemistry that we'd denied ourselves through dating was obvious now and it took us both by surprise. I pulled my shirt off and threw it behind me somewhere as Carolina sat on the bed in anticipation. I watched her eyes go to my bulge as I was taking off my belt. I hooked my thumbs into my underwear and pulled my pants down to knee level to step out of them. My straining cock flopped out directly in front of her face. Carolina's eyes got big and she did the only double take I've ever seen any person do in earnest. My dick is very large. Then she looked away as if considering the enormity of the situation. Looking back on it, this was one of the context clues she dropped that suggested that she hadn't had a lot of experience with guys in general -- but I'd be lying if I said that her reaction didn't give me a swelled head. Pun intended.

Rather than grabbing or sucking on my cock, after I stepped out of my pants she stepped up to me slowly and we continued making out. We had started to sweat a bit and I remember her perfume with a salty tinge as I nipped at her neck. She groaned lustfully and we fell back on the bed. I rolled over onto my back and she got up and straddled me. Her pussy was soaked -- I could feel the wetness on my cock. She sat up and pulled her sweater off. I'm pretty sure I had an equally wordless reaction of my own as, once freed, her tits were much larger than I'd estimated. My jaw dropped a bit but I sat up into her breasts before she could get her head free of her top. I swirled each hard brown nipple in my mouth listening for her sighs.

"Put it in."

I reached down between us and rubbed my cock along her wet slit a few times, getting myself ready to enter her. Then I pushed the head of my cock up into her... and stopped. I couldn't go any further. It was as if my cock had hit an unyielding wall. I'd taken my first girlfriend's virginity, so ostensibly I knew what that felt like. This was nothing like that. Carolina began to bounce up and down on my cockhead and was making frustrated little groans. My head was inside her pussy lips and it felt ok but then I'd hit the barrier and it was like fucking a wall. I was beginning to think this was going to end up being the worst sex I'd ever had.

Just when I was getting ready to call it off for fear of bending (or, god forbid, rupturing) my dick; I'd actually taken the breath to tell her to get off me -- Carolina came down on my cock and it punched through. I sunk into the tightest pussy I've ever felt, by far, she let out a yelled groan that still gets me hard just thinking about it. We both grinned at each other and the fucking began. I laid back on the bed while she rode my cock enthusiastically. She was moaning louder now and had pulled my hands to her tits, throwing her head back and enjoying herself. I myself was shocked -- typically I could hold out during sex for as long as I wanted, owing to always having been a death grip masturbator. But Carolina's tight vaginal walls were proving almost too much for me. I began to feel the tingle in my balls signaling my impending shot after about 5 minutes. I was making the effort to hold back when Carolina stopped, shrieking and quivering in a huge orgasm. Her muscles held my shaft firmly, preventing any movement. Fortunately, this also had the effect of forestalling my own nut.

When she came down and caught her breath she was looking at me in awe and started riding again. Within about two minutes she had another explosive orgasm that clamped down on my dick. This second time, though, I pushed in as hard as I could and this set off a violent shaking in her. She leaned forward and kissed me deeply after that. We slowed things down.

She got off me at that point and laid back on the bed with her legs spread while I put on a condom.

"Your turn. Go easy on me with that thing."

The rubber had a great delaying effect. It was still tight but the deadening of sensation allowed me to withstand her extremely snug pussy. I fucked her through two more orgasms, each one with a notable firm clasping grip on my dick, but being on top allowed for an easier drive through her taut vaginal walls. When I finally came during her fourth orgasm she screamed the loudest I'd heard from her that night. It was the best ball draining orgasm I'd ever had.

Lying there afterwards with huge smiles on our faces, she turned to me:

"You know, that wasn't funny at all."